140Afinalexamblank - Chemistry 140A Fall, 2004 Final Exam:...

Chemistry 140A Fall, 2004 Final Exam: 550 points 12/9/04 DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO. ....FILL OUT THE FOLLOWING INFORMATION NOW : TA first name (circle one): JOSH TONY AARON . YOUR NAME (Print): . SIGNATURE: . BY SIGNING BELOW, I REQUEST AND AUTHORIZE MY FINAL EXAM SCORE AND FINAL LETTER GRADE TO BE POSTED ACCORDING TO MY UNIVERSITY PID ON THE CLASS WEBSITE AUTHORIZATION SIGNATURE: . PID: . ID checker initials: . If you wish to have any answers considered for a re-grade, your exam must be completed in INK .

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1. (18 points) Draw the Lewis dot structure for the following species. In each case, all atoms must satisfy the octet rule (except hydrogen). Be sure to draw all valence electrons and indicate the appropriate charges on the correct atom where appropriate. For bonds between atoms, draw a straight line rather than dots. example: NO 2 (-) N O O (-) NO (+) H 3 O (+) HNO 3 (-) CO CH 3 NH 3 (+) HCC (-)

2. (30 points) Draw three resonance structures for the following molecule. HCONH 2 (oxygen is bonded to the carbon only) 3. (10 points) Draw the structure of the best resonance contributor: 4. (5 points) Give one reason why it is better than the other two. (one or two words only!): 5. (12 points) Draw the bond line formulas for all of the constitutional isomers of pentane, C 5 H 12 . 6. (3 points) Draw the bond line formula for the pentane constitutional isomer that would be expected to have the highest boiling point:

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7. (3 points) If you were to brominate a mixture of ALL of the constitutional isomers of pentane under free-radical conditions, how many different monobromo compounds could be formed? 8. (3 points) Of these, draw the structure of the monobromo compound that would be expected to form the fastest. 9. For the following compound: CH 3 CH 3 Br (a) (8 points) Give the IUPAC name: (b) (2 points) How many chiral centers does the molecule have? (c) (4 points) Designate the chirality of the bromine-bearing carbon: 10. (10 points) Draw a constitutional isomer of the compound of question #9 (above) consisting of a 1,4 disubstituted six-membered ring with a sec-butyl substituent. For each of the following reactions, draw the structure of the single, major

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